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> It sucks ass when your mail does not get through as GMail/Hotmail rejects a connection from the IP address your cloud company allocated for you, in spite of DKIM etc.

God, yes. Gmail, in particular, really enjoyed just dropping connections from my IPv6 addresses every few months. Sometimes it would return an error, something obtuse and wrong like maybe, "your forward and reverse DNS records do not match" even though they absolutely did and hadn't changed in years.

Outlook/Hotmail was far better and would always return a sane, yet sometimes inscrutable, error that bore some resemblance to reality. It still took them a week to get me off the hit list that I got dropped on for no discernible reason.

> Or they decide to mark your mail is "suspicious" and it goes into the recipient's Spam folder.

Gmail was the ABSOLUTE FUCKING WORST about this. My spouse's e-mail to Etsy customers who used Gmail--not spam, not newsletters, person-to-person e-mails INITIATED BY THE CUSTOMER--would work for the first couple of e-mails in a thread and then start going into spam. Or, even more fun, friends with whom either of us had e-mailed would send us a mail and then we'd reply and nope, into spam.

Gmail would do this for WEEKS and no amount of poking or begging or pleading would make it stop. And then it spontaneously would. So maybe the begging did work but was just delayed. I dunno. I tried signing up for Gmail's "Postmaster Tools" but no data was ever reported because "your mail volume is too low."

The ultimate ignominy? The final humiliation that sent me to Fastmail? I finally, through a couple of professional contacts, got to actually e-mail (via Gmail, of course, because they were blocking my personal domain again) with a real, live Gmail SMTP admin to ask why my latest round of e-mails were going into the bit bucket. Know what he said, even though my domain has been hosted on a server in the same colo facility with the same IP addresses for a decade? Something along the lines of "your domain reputation is coming back as too new."

Ladies and gentlemen, I give you whois:

google.com - Creation Date: 1997-09-15T04:00:00Z

mypersonaldomain-notreallythisvalue.org - Creation Date: 1997-03-10T05:00:00Z

> no data was ever reported because "your mail volume is too low."

That is fucking shameful indeed. Domains with tiny volume need postmaster tools the most…

But it seems like having a little conversation from your domain with a gmail address helps. Just send a mail to your google account, click not spam, reply, do a couple more back and forth replies.

Yes, dude, I feel you. I was there. I got the same shit. A few more examples of their wonderful software: - GMail sometimes accepted mail from IPv4 but not IPv6. - I rebuilt the VM running postfix, got a new IP address and then mail was blocked due to "IP address is known as dynamic end-user"

Worst of all, the mail does not always bounce... and when it does, this is no one to email and ask. What are mail admins supposed to do?

> "your domain reputation is coming back as too new."

Did you follow up on that crap and asked what the fuck could possibly be going on with this nonsense? (More politely than I just did of course.)

We chatted about it for a little more but he wasn't able to figure it out either, so I gave up and moved the three active users I had over to FastMail that evening. A handful of semi-used mailboxes are still on the other setup that I still keep trying to make work but not nearly with the same force and gusto as I used before.

I have had the same problems with IPv6 and Gmail. As I also admin G.Suite I have access to their paid support.

I did your exact follow up - politely and persistent!!

It was a dead-end. They had no idea - and worse - no escalation path to the SMTP team.

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